Acetic Acid → HCID 539410, compound

HRID 363803Notes

Reaction equation

HRID 363803 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[Br:6]N1C(=O)CCC1=O.[C:14]([OH:17])(=[O:16])[CH3:15]>>[C:14]([O:17][CH2:1][CH:2]=[C:3]([CH3:4])[CH2:5][Br:6])(=[O:16])[CH3:15]

Participants

4

Conditions

Temperature
15 °C

Procedure

Into acetic acid (500 ml) were dissolved 85 g (1.25 mol) of isoprene. Under stirring at 15° C., 260 g (1.45 mol) of N-bromosuccinimide were added therein dividedly four times little by little over two hours. Thereafter, the resulting mixture was stirred for additional two hours. The reaction liquid was added into ice water and extracted with ether. After the organic layer was washed with water, washed with a 5% aqueous solution of sodium hydrogencarbonate, washed with water and dried, the solvent was distilled off. The resulting residue was distilled under reduced pressure, whereby 115 g of the title compound were obtained. (Yield: 52.3%)

Workup

  1. stirringThereafter, the resulting mixture was stirred for additional two hours
  2. customThe reaction liquid
  3. extractionextracted with ether
  4. washAfter the organic layer was washed with water
  5. washwashed with a 5% aqueous solution of sodium hydrogencarbonate
  6. washwashed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. distillationThe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-8ad55d739623492397dc34d64a5329f0
Source dataset
uspto-grants-1999_02
Patent number
US05874611

Reaction notes

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